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Chesapeake Beach

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Vacation Rentals in Chesapeake Beach, MD

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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22 Trusted Chesapeake Beach Area Rentals
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-20 of 22
Top of the Chesapeake - Near Historic Charlestown, Chesapeake Beach
United States, Maryland, Chesapeake Beach Holiday Rentals
Top of the Chesapeake - Near Historic Charlestown
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 6 Bedrooms, sleeps 13
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
163 AUD - 440 AUD
Week:
1,128 AUD - 2,666 AUD
Minimum rental - 1 night
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The following rentals are within 30 kilometres of Chesapeake Beach, Maryland.

1920's restoted waterman's cottage with fantastic views!, Tilghman - JUST ADDED
United States, Maryland, Tilghman Holiday Rentals
1920's restoted waterman's cottage with fantastic views!
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
363 AUD - 438 AUD
Week:
1,719 AUD - 2,301 AUD
Month:
6,485 AUD - 7,951 AUD
Minimum rental - 2 nights
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1 bedroom cottage near water with artist studio, North Beach
United States, Maryland, North Beach Holiday Rentals
1 bedroom cottage near water with artist studio
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 1 Bedroom, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
128 AUD - 190 AUD
Week:
770 AUD - 975 AUD
Month:
2,566 AUD - 3,592 AUD
Minimum rental - 2 nights
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Black Walnut Point Inn, Tilghman
United States, Maryland, Tilghman Holiday Rentals
Black Walnut Point Inn
Slideshow
4.5 of 5 stars 4 reviews
  • Guest Room
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
282 AUD - 359 AUD
Week:
1,411 AUD - 1,796 AUD
Minimum rental - 1 night
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Grandview Mainhouse, Bozman
United States, Maryland, Bozman Holiday Rentals
Grandview Mainhouse
4.5 of 5 stars 6 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 13
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
544 AUD
Week:
2,053 AUD - 2,822 AUD
Minimum rental - 1 week
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Cottage in Heart of St Michaels--Walk Everywhere!, St. Michaels
United States, Maryland, St. Michaels Holiday Rentals
Cottage in Heart of St Michaels--Walk Everywhere!
Slideshow
4 of 5 stars 1 review
  • Holiday Rental House
  • 2 Bedrooms, sleeps 5
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Night:
103 AUD - 359 AUD
Week:
975 AUD - 1,488 AUD
Month:
1,796 AUD - 4,464 AUD
Minimum rental - 2 nights
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Bay Cottage Waterfront Vacation Estate, St. Michaels
United States, Maryland, St. Michaels Holiday Rentals
Bay Cottage Waterfront Vacation Estate
Slideshow
4.5 of 5 stars 3 reviews
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 6 Bathrooms
  • Owner
EMAIL OWNER
Night:
821 AUD - 1,283 AUD
Week:
4,002 AUD - 5,850 AUD
Month:
11,802 AUD - 19,294 AUD
Minimum rental - 3 nights
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Restored 1920s Cottage: Great Home Base for Exploring Eastern Shore Villages, Claiborne - JUST ADDED
United States, Maryland, Claiborne Holiday Rentals
Restored 1920s Cottage: Great Home Base for Exploring Eastern Shore Villages
Slideshow
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Professional
EMAIL AGENT
Night:
225 AUD - 286 AUD
Week:
1,295 AUD - 1,522 AUD
Month:
4,521 AUD - 4,816 AUD
Minimum rental - 2 nights
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Hidden Cove Apartment resting on the Shores of Wells Cove, Saint Leonard
United States, Maryland, Saint Leonard Holiday Rentals
Hidden Cove Apartment resting on the Shores of Wells Cove
Slideshow
  • Condo/Apartment
  • 1 Bedroom, sleeps 2
  • 1 Bathroom
  • Professional
EMAIL AGENT
Night:
92 AUD - 128 AUD
Minimum rental - 2 nights
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Chesapeake Bay! Fabulous Views! WATERFRONT APT!, Taylors Island
United States, Maryland, Taylors Island Holiday Rentals
Chesapeake Bay! Fabulous Views! WATERFRONT APT!
  • Condo/Apartment
  • 2 Bedrooms, sleeps 8
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
128 AUD
Minimum rental - 1 night
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Private waterfront cottage with deep water dock, great location, Bozman
United States, Maryland, Bozman Holiday Rentals
Private waterfront cottage with deep water dock, great location
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL AGENT
Night:
427 AUD - 682 AUD
Week:
2,092 AUD - 2,582 AUD
Month:
8,360 AUD - 8,542 AUD
Minimum rental - 2 nights
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Maryland Eastern Shore Waterfront Estate, Oxford
United States, Maryland, Oxford Holiday Rentals
Maryland Eastern Shore Waterfront Estate
Slideshow
  • Holiday Rental House
  • 8 Bedrooms, sleeps 16
  • 6 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
452 AUD - 997 AUD
Week:
3,233 AUD - 6,979 AUD
Minimum rental - 2 nights
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Unexpected touches! Turn key retreat convenient to Easton and St. Michaels, Royal Oak
United States, Maryland, Royal Oak Holiday Rentals
Unexpected touches! Turn key retreat convenient to Easton and St. Michaels
Slideshow
  • Holiday Rental House
  • 4 Bedrooms, sleeps 8
  • 4 Bathrooms
  • Professional
EMAIL AGENT
Night:
422 AUD - 583 AUD
Week:
2,205 AUD - 2,856 AUD
Month:
9,134 AUD - 10,561 AUD
Minimum rental - 2 nights
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Estate property biking distance to town. Pool, private grounds, dock., Oxford
United States, Maryland, Oxford Holiday Rentals
Estate property biking distance to town. Pool, private grounds, dock.
Slideshow
  • Holiday Rental House
  • 5 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL AGENT
Night:
601 AUD - 1,149 AUD
Week:
2,990 AUD - 5,633 AUD
Month:
14,702 AUD - 22,058 AUD
Minimum rental - 2 nights
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1747 Georgian House Historic District, Annapolis
United States, Maryland, Annapolis Holiday Rentals
1747 Georgian House Historic District
  • Holiday Rental House
  • 4 Bedrooms, sleeps 11
  • 4 Bathrooms
  • Owner
EMAIL OWNER
Night:
770 AUD
Week:
5,131 AUD
Minimum rental - 1 night
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North Beach Boardwalk Bayfront Cottage Chesapeake, North Beach - JUST ADDED
United States, Maryland, North Beach Holiday Rentals
North Beach Boardwalk Bayfront Cottage Chesapeake
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 9
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
262 AUD
Week:
1,411 AUD
Month:
3,079 AUD
Minimum rental - 2 nights
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Cottage 2 at Grandview Pleasure Point, Bozman
United States, Maryland, Bozman Holiday Rentals
Cottage 2 at Grandview Pleasure Point
Slideshow
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
282 AUD
Week:
924 AUD - 1,411 AUD
Minimum rental - 1 week
Check availability
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HGTV Home on MDs Eastern Shore, Sherwood
United States, Maryland, Sherwood Holiday Rentals
HGTV Home on MDs Eastern Shore
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 6
  • 4 Bathrooms
  • Professional
EMAIL AGENT
Night:
616 AUD - 835 AUD
Week:
3,315 AUD - 5,007 AUD
Month:
14,796 AUD - 19,432 AUD
Minimum rental - 2 nights
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1-20 of 22

Chesapeake Beach Holiday Rental Advice

Why are there no hotels in Chesapeake Beach, Maryland?
Posted by spachick, 29 Jun 2008
... I see beautiful beach front condos for sale, it makes me why anyone would want to sell in such a beautiful place. You also gave me some interesting information because I didn't know there was a commuter bus from DC to NB. Wish I could rent your home but ... more
Posted by IrishFan, 29 Jun 2008
... I see beautiful beach front condos for sale, it makes me why anyone would want to sell in such a beautiful place." Possibly because they were purchased by investors looking to make a quick flip on the condo. With the downturn in the market that isn't going to happen ... more
Posted by Borracho, 29 Jun 2008
Some of the condos over there in North Beach have never been purchased. At least not in the 3 years we've been here. The views are great but I don't know that the over 450K price tag is worth it - even with the view. On my street alone ... more
Young children
Posted by KER000, 17 Jul 2007
I am going here for a wedding and can't find anywhere else to stay other than the chesapeake beach resort & spa. We would stay in another hotel or perhaps a house/condo. Please let me know some other choices I have. Thank you! ... more
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